Good Leaders Fail Well

How Mistakes Become a Staircase

As a younger man, I expected that leadership would mean responsibility, burden, and difficult decision-making. I didn’t know, however, that leadership would also mean a good deal of failure.

I don’t have in mind large-scale, shocking failures — the kind that disqualify a man from pastoral ministry, for example. No, I mainly have in mind more common trips and stumbles, sometimes sinful, sometimes not — the kind that leave the self-aware leader often looking back embarrassed, wishing he had done or said something different.

I have in mind sermons that come out flat and land even flatter. Bible-study discussions that whimper and die. Public jokes told unwisely; public judgments spoken hastily. New ministry initiatives that run, then stagger, then stumble, then fall. Decisions that, in hindsight, were dead wrong. Younger Christians who find more help somewhere else.

Stepping into leadership means stepping into mistakes, regrets, and many small but stinging failures. And surviving in leadership, I am learning, means stepping upward on those mistakes — owning them, learning from them, and having the stability in Christ to keep leading after them.

Leaders Fail

To some extent, of course, every fallen human is familiar with failure. Mistakes follow us from the womb; we learn regret alongside the alphabet. But for at least two reasons, leadership has a special way of drawing failure to the surface.

First, leadership provides a public platform for the kinds of mistakes we were already making. Surely Moses made blunders while building a family in Midian, and David while shepherding his father’s flocks, and Peter while fishing the Sea of Galilee. But their mistakes were more or less private — pebbles tossed into the pond, their ripples small and few.

But then Moses began building a nation, David began shepherding a kingdom, and Peter began fishing for men. And all of a sudden, their private failures became public and subject to greater scrutiny. We need not have a large leadership platform to experience the same kind of uncomfortable exposure. Once we failed behind closed curtains; now we stand upon the stage.

And then, second, leadership affords many more opportunities for failure than we had before. Among the family, among the sheep, among the fish, opportunities for failure were present but more limited. When leadership called Moses and David and Peter out of those worlds, worlds where they felt some semblance of success and control, their chances of failure multiplied.

Leadership, at its heart, involves public initiative and risk-taking. Leaders try new ventures; they aim, by God’s grace, to bring new realities into being; they call people to follow down paths not yet trod. And sometimes, the efforts of even the best leaders fall apart, and the risks return to smack them in the face.

Two Common Paths

A few failures and mistakes sting. A few dozen wound. And then, over time, as mistakes rise even higher, we may feel ourselves standing before a mini-mountain of regret — a monument, it may seem, to our incompetence. At this point, two paths may tempt a leader.

The first temptation is to protect ourselves from the vulnerability of leadership by wearing a cast-iron cloak. Criticism no longer reaches our skin. Failures no longer wound because we refuse to feel them. And slowly, the once-lowly son of Kish becomes proud King Saul, hard and high, safe from the sting of failure — and safe too from the grace of God.

The second and perhaps more common temptation is to run away. Ditch. Flee. Follow Peter back to Galilee, back to the fishing boat, back to some private sphere where no one is watching and I know what I’m doing (John 21:3). Or alternatively, keep “leading,” but stop trying so hard. Leave risks unattempted and hills untaken. Lead from the land of Safe.

“If every leader stung by failure stepped away, the church would have no leaders.”

Now, stepping away from leadership is not always wrong. Maybe, in the wake of some particularly jarring failure — or after a longer pattern of missteps — we really do need to step back for a season and find our identity again in unhurried communion with Christ. Maybe we’ll start leading again after a time. Or maybe, through much prayer and counsel, we’ll decide not to return to formal leadership. And in some cases, that would be okay. The body of Christ has many members, a handful of whom are leaders, all of whom are indispensable (1 Corinthians 12:22).

Nevertheless, if every leader stung by failure stepped away, the church would have no leaders. Somehow, then, we need another way, a way of treating mistakes like so many stairs upon which, over time, our Lord raises us into more faithful and fruitful leadership. We need grace to see not only how leaders make mistakes, but how mistakes can make leaders.

Every Failure a Stair

In his kindness, God filled his Scriptures with stories of leaders who failed but didn’t finish there, who crashed but didn’t burn. Yes, we read here of men like Saul and Judas and Demas, leaders whose failures made their graves. But we also read of men like Moses and David, Peter and the other disciples, whose maturity as leaders rose on a staircase made of failure.

“We need grace to see not only how leaders make mistakes, but how mistakes can make leaders.”

We may find help from Peter in particular. His three-part collapse may have been a bigger failure than the kind we have been considering, but his story still gives us categories for how we might step upward on our own failures, however large or small.


The morning of Good Friday revealed more of Peter than Peter had ever seen. Just the night before, he swore he would die before he denied Jesus; then one, two, three: “I do not know him” (Luke 22:57). The rooster crowed. Jesus looked. And Peter, in that one swift moment, saw himself for who he was.

Instead of fleeing from such agonizing knowledge, though, he owned it. First, “he went out and wept bitterly” (Luke 22:60). Then he returned to his friends (Luke 24:10–12). And then, finally, on that early-morning Galilean shore, he offered no rationalization, no justification, no excuse (John 21:1–17). Failure had owned Peter on Good Friday — and here, standing before his gracious Lord, Peter owns his failure.

Sometimes, of course, our failures are matters more of weakness than of sin. Perhaps failure reveals not our guilt but our immaturity, our ignorance, our incompetence in certain areas. Either way, the process still uncovers parts of us we need to see, sometimes desperately. Therefore, fully owning our failures is still the path of humility and wisdom. Receive them. Embrace them. When others look around for someone responsible, let them see us raising our hand.

The strength for such a painful embrace comes, in large part, from the confidence that failure lies well within God’s sovereign plans for our good. Without failure, Peter would have remained self-confident and self-deceived; so would we. And so, in his sovereignty, Jesus sometimes allows his people to pass through the sift of failure (Luke 22:31–32). He does not, however, keep them there.


If we, with Peter, feel the sting and refuse to run, we will find a future beyond failure. We also will find that failures speak a thousand lessons to those who are willing to pause, look them in the face, and ask them to teach us.

Too often, I allow the pain of the present moment to keep me from learning from failure. Today, the failure hurts. Today, I feel embarrassed. Today, I would rather soothe or distract myself than take my mistakes by the hand. I forget that, in failure, God often has tomorrow in mind.

“When you have turned again,” Jesus tells Peter, “strengthen your brothers” (Luke 22:32). Jesus knew that when Peter turned again, hollowed and then healed, he would be a different Peter. Outside that dark courtyard, self-confidence drained from Peter like so many bitter tears. And on that Galilean shore, love for Jesus rose in Peter like a miraculous catch of fish. Failure today made Peter an apostle tomorrow — now so much stronger in Christ, now so much more wary of self. But only because he learned from failure.

Sometimes, replaying our failures leads only to a fresh sense of shame or condemnation. But what if we returned to the scene not alone and exposed, but alongside our forgiving Lord? And what if we asked him to help us review our failures with an eye toward tomorrow? We might find that errors become humility, mistakes become maturings, regrets become wisdom, self-inadequacy becomes Christ-sufficiency, and failures become reliable stairs.

Keep Leading

Having owned our mistakes and learned what we can from them, we might imagine Jesus lifting us up from the ground, looking us in the eye, and offering both a question and a call.

“Do you love me?” he asks Peter (John 21:15–17). Before the failure, Peter’s love was real but shallow; now, as his risen Redeemer restores him, his love is real and deep. Amazingly, failure can do the same for us — taking the love of Jesus from theory to reality, taking our love for Jesus from frail to strong.

The question also sets Peter, and us, on firmer ground. If leadership is mainly about us — our praise, our validation — then failures will either send us running away or wrapping that cast iron around our hearts. But if leadership is ultimately about Jesus — his worship, his worth — then we can make ourselves vulnerable again for him. Yes, we have failed. Yes, we may fail again, and feel again all the pain of falling on our face. But we love him. And love can risk being broken.

Finally, having asked us the question, he bids us to respond again to the call we heard so long ago: “Follow me” (John 21:19). Prepare the next sermon. Plan the next meeting. Chart the next course. And by a miracle of grace, keep leading.